I cant comment on "sharing" an airplane...I'm WAY too protective for something like that. I get mad enough when I track dirt into the cabin, let alone someone else.
I went straight from my 150 to the Warrior that I have now. I have NO regrets at all, I am happy as can be! I do miss flying low and slow 300-400 ft and watching the kids wave when I would fly by. But I do like the idea of having nearly 6.5 hours fuel range and more useful load. Also, having a wife and two kids make the Warrior a more practical plane.
If you shop and find one that has been kept out a lot, make sure you check the spar attach fittings. The window seal on the pilots side can leak allowing water to trickle down and rust out the steel attachments.
Given your choices, I'd rather have a 150 all to myself than have a quarter share of a Cherokee.
